


Giving Into Urges

by LightLeadingMe



Series: Friends Shouldn't Kiss Like We Do [1]
Category: Will & Grace
Genre: F/M, Fooling Around, Friends With Benefits, Friendship, makeout sessions, slightly smut?, will eventually be smut
Language: English
Status: Completed
Published: 2018-04-30
Updated: 2018-05-05
Packaged: 2019-04-30 00:12:51
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 3,642
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14484345
Author URL: https://archiveofourown.org/users/LightLeadingMe/pseuds/LightLeadingMe
Summary: 'Friends should sleep in another bed, and friends shouldn't kiss me like you do...'Jack and Karen take their normal fooling around one step further than they ever have before.





	1. Chapter 1

Jack always knew that he could turn Karen on. He knew since he first touched her back when he wanted to be a massage therapist not too longer after they met. It only became more obvious when he'd ask to kiss her and she never even hesitated to comply. She would let him do anything he wanted to her. She didn't care about her husband or the person she happened to be with at the time. She wanted him and he knew it.

He would never admit it, but Jack liked to use this power he had over Karen to his advantage. Like last week when she took him shopping with her and he really wanted a particular pair of jeans, but Karen refused, reminding him she had just bought him a pair the week prior and he still had yet to wear them. He begged her to at least see how great his ass looked in the jeans, inviting her into the dressing room with him. She had rolled her eyes, but as soon as she stepped into the small space, Jack pushed the door shut and kissed her, backing her into the wall. He grabbed her wrists and brought her hands around to his ass, smiling against her mouth when he felt her squeeze.

"See?" he mumbled, their lips still connected.

"Mmm," she moaned, tilting her head to the side, her tongue brushing his lips.

Twenty minutes later they walked out of the store, Jack's new jeans in one of the many bags they had, both of them with satisfied grins on their faces, but for very different reasons.

Then there were times when Jack just felt like kissing her. He couldn't explain it at all, but he'd be sitting next to her on the couch in his apartment, watching as she told him a story or just idly drank her martini, her eyes fixated on the television, and he just felt such an urge to take her in his arms and kiss her.

On a warm Friday night, they were in Karen's bedroom. The balcony doors were open, letting the summer night air breeze into the room as the curtains swayed in a dance with the wind. Karen perched in the middle of the bed, looking down at some photographs Jack had found in the closet where he was snooping while Karen was yelling at her staff. He lay next to her, his head in her lap, handing her photos, curiosity coursing through him, and she explained and answered any questions he had about each memory. He watched, fascinated by the gleam in her eyes as she spoke him and he found that all too familiar urge rise within his chest. He sat up, taking the photo from her hand gently and set it aside. Karen opened her mouth to question him, but he cut her off with his tongue as it slipped between her lips, seeking hers out almost desperately.

He felt Karen's hands course through his hair, her fingers tugging as the short strands on his neck. He turned his body, his hands on her back guiding her to lay down, his body hovering over her. He ran his hands all over her, caressing and delighting in the feel of the silk of her nightgown and the soft curves of her body beneath his fingertips. He loved this nightgown on her; he even helped her pick it out. It was a cream color, short with a slit up to just below her hip. Her bosom was low cut and covered by only a thin layer of lace, just enough to see the pink of her nipples.

He loved her breasts. His face had been between them many times; whether he was motorboating her or just cuddling, he loved the feel of them against his cheeks. He slid one of his hands from her hip to her tits, his palm not large enough to cover her full breast, and he massaged it, just the way he knew would get her worked up. She mewled into his mouth, her back arching to press her chest further into his hand. He trailed his lips down her neck to her collarbone, his teeth nibbling and his lips sucking at the exposed area. Karen raised her leg up and hooked her ankle behind his calf, bringing his leg between hers so his jean clad thigh was pressed perfectly against the apex between her thighs.

Jack lifted his head from her neck, a surprised look on his face. This position was new. Karen peered up at him through hooded eyes, her green orbs filled with desire. Feeling a boldness he never felt with any other woman before, Jack shifted and pressed his thigh further into her, aware of the heat radiating from between her legs. Karen gasped, her eyes widening at the sensation of his muscular thigh applying the perfect amount of pressure to her clit.

For a moment they just stared at each other. His hand was still on her breast and he could feel her rapid heart beat beneath his palm, both their chests heaving breathlessly from their deep kisses. He could practically see the questions running through her mind, but he himself didn't know what was happening. He finally tore his eyes away from hers and scanned down her neck and shoulders to her chest, as if he was mesmerizing the way she looked in this moment. He curled his fingers that were resting on her breast and yanked down on the material of her nightgown, exposing a perky pink nipple to his hungry eyes. Without hesitation, he leaned down and captured the nub in his mouth, his tongue laving ravenously at the hardened nipple.

Karen gasped again at the sensation and before she could stop herself, she began rotating her hips in a circular motion, grinding against his leg. She was soaked, breathless, and in dire need of a release. Jack, taking note of her movements, pressed himself even closer to her, his mind curious and desperate to see what she looked like when she came.

Never releasing his lips from her tit, he lifted his eyes to watch as her eyes fluttered and her hands grasped at the pillow beneath her head. He bit down gently and used his other hand to pinch her neglected breast, still covered by lace. Karen cried out and then shuddered, gasping as she rode the waves of her orgasm. Jack felt her release on his jeans, a wet spot now marked on his thigh. He pulled his lips away from her nipple and a 'pop' sound from the suction seemed to echo in their ears. He grinned like the cheshire cat as he watched his satisfied friend catch her breath, a moan or two still escaping her kiss bruised lips.

"Damn," she muttered finally, opening her eyes to catch his. "What the hell just happened?"

Smirking, Jack looked thoughtfully down at her. "I believe you just had what we call a 'lady-gasm'. It's when the female, such as yourself-"

She smacked his arm and they both erupted into a fit of giggles. Jack rolled off of her and onto his back, trying to ignore the fact that she got off and he didn't. As if reading his mind, he felt Karen toss a leg over his upper thighs so she was straddling him. Her nightgown was still out of place, the straps now loosely down around her biceps and one of her tits still exposed. She had her hands on his chest, her fingers drawing small circles over the hard muscles there.

"Jackie?" she asked sweetly. "Has a woman ever given you a blow job?"

He frowned, only slightly. "No." He glanced up and saw the gleam in her eyes, a dirty grin spreading across his lips to match hers. "But there's a first time for everything, right?"


	2. Chapter 2

Karen couldn't believe this was happening. She was straddling her gay best friend, her nightgown askew, hair mussed, and body still shaking occasionally from the aftermath of her orgasm. Jack peered up at her with an indifferent look in his eyes.

"Jackie?" she asked sweetly. "Has a woman ever given you a blow job?"

He frowned, only slightly. "No." He glanced up and Karen watched as the dirty grin washed over his face. "But there's a first time for everything, right?"

Her heartbeat raced and she nodded at him. She began to tug at his shirt as a signal for him to take it off. Jack got the hint and sat up, lifting his arms above his head so Karen could pull the shirt off him. She tossed the garment to the side and bit her lip, appreciating the muscles that adorned his upper body. Raising herself up on her knees, Karen kissed him, her nails scraping gently along his pecs and down his abs. Their tongues battled roughly and she smiled against his mouth as a whimper escaped him when her hands finally reached his belt buckle. She parted from the kiss and shoved him back so he was once again lying down.

Karen unbuckled his belt and unzipped his jeans, her finger tracing the bulge beneath his navy blue boxers. She slipped her hand into the small opening at the front and caressed his already hardening cock slowly. Jack sighed in content, but wiggled his hips, his hands pushing at the material constricting Karen from touching him fully.

Taking the hint, Karen tugged as Jack raised his hips, sliding his jeans and boxers down and off his body. At the sight of his well endowed erection, she let out a low moan, her mouth practically watering. She had seen him countless times before, but never like this, and never with permission to suck him off. She wrapped her fingers around him and licked the tip, not wanting to waist any more time. Jack hissed above her and she smirked before wrapping her lips around the head of his cock, her tongue swirling while her hand began to stroke him leisurely.

"K-Karen," Jack gasped. "Oh my God..."

She felt one of his hands creep into her hair, his fingers tightening around her dark locks. Karen glanced up and removed her hand from him, placing it next to his hip on the mattress. She waited until he looked down at her and when their eyes locked, Karen relaxed her throat enveloped his entire length into her mouth. Karen Walker didn't kid around when it came to blow jobs and she was determined to give Jack the best head of his life. She bobbed her head a few times, feeling him tap the back of her throat, and her tongue traced the vein on the underside of his cock, causing Jack to involuntarily thrust up.

Karen released him from her mouth and her hand returned, stroking him up and down, her pace quickening as she licked her lips seductively while he watched. He tugged at her hair and she brought her mouth back down to him, her head bobbing back and forth in perfect synchronicity with her hand.

Feeling her own arousal now practically pour out of her, Karen reached between her legs, never faltering in her movements, and slipped her hand into her panties, two fingers burying into her pussy. She moaned against him as she began to rapidly pump her fingers in and out in time with the hand on his throbbing member, wanting to cum with him.

She looked at his face again and as soon as he caught sight of her hand between her legs she felt his is cock twitched in her mouth and his legs tense up.

"Oh, I'm gonna cum," he moaned, throwing his head back against the pillow

Karen tightened her lips around the head of his cock as her hand sped up and then jets of cum shot down her throat. Jack was gasping and sighing happily as he came and Karen released him from her mouth, her hand still stroking him slowly as she felt the familiar tightening in her stomach. She squeezed her eyes shut and curled her fingers even further, knuckle deep, and cried out in ecstasy. She came so hard that her juices soaked her hand and panties, dripping onto Jack's thighs.

It took a few moments, but she finally caught her breath and collapsed next to him on the bed, feeling satiated and relaxed. She glanced up at Jack who was staring down at her with a grin.

"Wow," he said. "That was amazing, Kare."

She winked and reached out to pat his chest. "I am to please, honey..." It was silent for a bit, neither of them sure if they should talk about what just happened or if they should let it slide like most of their inappropriate escapades. "Hey Jackie," Karen spoke up, a curious thought springing to mind. "Who were you thinking about so you could get hard?"

"What?" Jack asked, a look of genuine confusion covering his face.

"Well, remember a few years ago when we did that 'inappropriate workplace' video crap and we tongued each other's ears?" She waited for him to nod in remembrance before continuing. "You told me to keep my boobies away so you could imagine Matt Damon, so, I figured that just now you had to-"

"You."

Karen stared at him, shocked. "Wait what-"

"I didn't have to picture anyone, Kare..." he confessed quietly, his fingers grazing her chin lovingly.

She bit her lip and look across the room, not sure where to go from here.

"Huh..."


	3. Chapter 3

"We should probably talk about this."

"Yeah, probably."

"I mean, I'm gay."

"That you are."

"But damn, that was amazing."

"I told you I was good, honey."

"So, even though I'm gay... why am I not freaking out right now?"

That, she didn't have an answer for. Jack turned his head and stared at his best friend. Her hair was beautifully fanned out over the pillow, her lipstick smudged, her nightgown twisting to one side, her tit still hanging out and the most confused look written across her face.

"Can I tell you a secret, honey?" she asked, her eyes fixated on the ceiling. "Do you remember when you first kissed me in Will's office six years ago?"

Jack smiled fondly at the memory and turned on his side, ignoring the fact that he was completely naked and she was still partially dressed. He was never shy before there was no need for him to be now. "Of course I do!"

Karen licked her lips, almost tentative to say the next part. She sighed and mustered up the courage, still keeping her eye line away from him. "Did you know I fainted after?"

Jack's jaw dropped and he felt a flutter in his chest. "You fainted?" He held a hand to his chest dramatically, a sense of pride enveloping him. "I mean I knew I was a good kisser, but damn!"

Karen finally glanced at him, still unsure of this conversation and a look of disappointment covering her features. "You don't get it, honey." She sat up, reaching to the front of her nightgown and tucking her boob back in. She ran a hand through her hair and sighed, locking her eyes on his confused face. "I've wanted you for years, Jack. Since you first touched me when you wanted to be a massage therapist I've wanted you. God, that was like the first time I had ever been touched in my whole life. You make me feel special, you make me feel beautiful..." She let out a humorless chortle before continuing. "Honey, you've been the light of my life these past few years." She saw him open his mouth and she placed a finger over it, hushing him before he could interrupt. "I know you know, poodle. I'm not exactly opaque when it comes to you."

"Karen," Jack sat up as well, placing a gentle hand on her shoulder. "You're right, I did know... but why are you telling me this?"

She stared at him her eyes darting all over his adorably puzzled face, her teeth biting her bottom lip so hard she was sure she was going to draw blood. "I'm telling you this because I want to ask you to do something for me that would change both of our lives..."

Jack's eyebrows furrowed together even further until it dawned on him what she was silently asking. "K-Karen, I don't know if I can..."

Unexpected tears sprang to Karen's eyes and she nodded, looking down at her hands as they fiddled in her lap. "No, of course!" she breathed out. "I knew that. It was silly of me to even..." She trailed off, the first few drops now dripping down her cheeks. She cleared her throat and turned her body away from him, swinging her legs off the bed so she sat on the edge. "Well hey, at least we both got a little something tonight, right?" She sniffed and closed her eyes, trying as hard as she could to keep her emotions at bay.

Jack scooted himself over to her. He spread his legs so they were on either side of her legs and wrapped his arms around her waist, pressing his chest against her back and laying his head on her shoulder. "I love you so much, Karen," he whispered and he felt a sob wrack her tiny body. Her hands rest upon his on her stomach and she squeezed. "I have a secret too." Karen turned her head to look at him and his heart ached at the sight of her tear stained face. He reached a hand up and stroked his thumb across her cheek, staring deeply into her eyes. "I never had to imagine James Van Der Beek when I kissed you." Her eyes widened and she began to sputter at him, but this time it was he who placed a finger over her lips to not interrupt. "Believe me, I tried," he confessed. "But when I look at you... it's only you. Don't get me wrong, I love sleeping with men, I do, but you are the only woman in the world that I've ever been attracted to, Karebear."

"Then why can't you-"

"Because I don't want to hurt you."

"Jack," she shook her head. "I've been hurting for years."

He pressed his forehead against her temple, closing his eyes as she sighed in his arms. "We're fucked up, Kare."

Her shoulders shook with laughter. "You can say that again, honey."

They stayed there silently for a little longer until Jack turned his head into her neck and placed tiny kisses along the skin he found there. Karen tilted her head to give him better access and then felt him rub up against her, his cock stiff against her back. "Whoah, honey," she gasped and pulled away to catch his eye again. "Are you sure?"

"Are you?"

They both slowly nodded and then their lips came together. The angle was awkward with him behind her so Karen stood up from the bed and turned around so she was standing between his legs. She pulled the straps of her nightgown and tugged the material until it fell around her ankles, making sure her panties went with it. Jack stared in awe of her body, his cock at full attention. Karen climbed onto the bed and crawled to the middle, laying on her back and biting her lip in anticipation.

Jack made his way over to her so he was hovering above her, resting his weight on her forearms on either side of her head. Karen raised her knees up and he lowered his body down slowly until he felt his cock brush against her entrance. They both gasped at the feeling, their eyes locked. She slid her hands down his sides placing them on his lower hips, her fingers brushing the sides of his ass and she lifted her hips as she guided him down. His cock entered her and they gasped simultaneously, their bodies shaking at the feeling of finally being connected. Jack leaned down and kissed her, pulling his hips back and thrusting into her again, finding a rhythm. They moved at a leisurely pace, not wanting to rush anything because they knew this would be the only time they could be together like this. At one point, Jack completely stopped, his cock still buried in her and they just shared gentle kisses and whispers of love.

He eventually picked up the pace and admired Karen's face as pleasure took over. When she began to close her eyes, Jack slowed down and her eyes snapped back open. "Look at me, Karen," he pleaded. "Don't look away."

Karen nodded and he began moving again, his hips thrusting faster than before. He pressed their foreheads together and they kept their eyes locked. Karen wrapped her arms around his shoulders and felt the beginnings of her orgasm. Tears once again sprang to her eyes and then she was flying, her body stiff and her walls contracting, milking Jack for everything he had. Jack was gasping as he came, overwhelmed by the feeling of her cumming around him, but their eyes never drifted.

After a few more thrusts, he broke their eye contact by kissing her before he collapsed on top of her. Karen anchored him to her chest, her fingers running through his hair as they caught their breaths. She felt his tears on her skin, mirroring the tears on her cheeks and he stayed seated inside of her for a few minutes. Neither of them spoke, they didn't need to; they said everything already.

They just stared out the window of Karen's balcony, watching as the sun began to rise over the the buildings of the city.

**Notes for the Chapter:**

> Well that's it on this little ficlet!! Hope you all enjoyed. :)


End file.
